Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → racemic ethyl 5-[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)-2H-indazol-6-yl]-5-(methylsulfonyl)pent-2-enoate

Participants

Reaction Steps

To a solution of an approximately 1:1 mixture of racemic 5-cyclopropyl-N-methyl-2-(4-methylphenyl)-6-[1-(methylsulfonyl)-3-oxopropyl]-2H-indazole-3-carboxamide (v) and compound (vi) (16 mg, 0.036 mmol) in DCM (10 mL) under argon was added ethyl (triphenyl-λ5-phosphanylidene)acetate (20 mg, 0.057 mmol), and the reaction was stirred at RT under argon for 1 h. The reaction mixture was evaporated to dryness and purified by flash column chromatography eluting with EtOAc/heptane (50-100%) to give racemic ethyl 5-[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)-2H-indazol-6-yl]-5-(methylsulfonyl)pent-2-enoate (vii) as a mixture of E and Z isomers (≈4:1) as an oil (18 mg, 99%).

Provenance & Evidence